Synthesis of bicyclic vinyl triazenes by Ficini-type reactions. Issue 37 (9th September 2021)

• Record Type: Journal Article
• Authors: Bormann, Carl Thomas; Fadaei-Tirani, Farzaneh; Scopelliti, Rosario; Severin, Kay
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 37(2021)
• Page Start: 8113
• Page End: 8117
• Publication Date: 2021-09-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01546j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Cyclobutenyl triazenes are obtained by Lewis acid-catalyzed [2 + 2] cycloaddition reactions of 1-alkynyl triazenes and enones. The triazene group in the product enables rearrangements and functionalizations. Abstract : Cyclic olefins with triazene functions can display interesting reactivity, but synthetic access to these compounds is limited thus far. Herein, we describe the synthesis of cyclobutenyl triazenes fused to cyclopentanone or cyclohexanone rings. The bicyclic compounds are obtained by Lewis acid-catalyzed [2 + 2] cycloaddition reactions of 1-alkynyl triazenes and enones. In the presence of Me2 AlCl, bicyclic [4.2.0] triazenes rearrange into [3.2.1] ring systems. The triazene function in the latter can be used for further functionalizations. Notably, we show that vinyl triazenes can serve as substrates for Pd-catalyzed cross-coupling reactions with arylboronic acids.